Stereoselective Synthesis of α-Disubstituted ß-Homoprolines.
Org Lett
; 25(38): 7067-7071, 2023 Sep 29.
Article
em En
| MEDLINE
| ID: mdl-37729003
ABSTRACT
An efficient enantioselective synthesis of chiral α-disubstituted ß-homoprolines was developed, starting with the stereodivergent allylation of chiral N-tert-butanesulfinyl imines derived from 4-bromobutanal with indium or zinc and using well-established and reliable synthetic transformations. This methodology allows the easy introduction of different substituents at the α-position of the pyrrolidine scaffold and is characterized by the possibility of switching the absolute configuration of the newly formed stereocenter either by changing the configuration of the tert-butanesufinamide chiral auxiliary or by using a different stereodivergent allylation protocol with the same auxiliary.
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MEDLINE
Idioma:
En
Ano de publicação:
2023
Tipo de documento:
Article